A practical synthesis of a key intermediate for the production of β- lactam antibiotics

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7779-7782

  Cainelli, Gianfranco ^a   Galletti, Paola ^a   Giacomini, Daria ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINONE DERIVATIVE; BETA LACTAM ANTIBIOTIC; BUTYRIC ACID DERIVATIVE; CARBAPENEM; TRIAZINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032532575     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01700-6     Document Type: Article

References (24)

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2. 1. Mickel, S. Aldrichimica Acta 1985, 18, 95. Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. Comprehensive review: Berks, A. H. Tetrahedron 1996, 52, 331 and references cited therein.
3. 1. Mickel, S. Aldrichimica Acta 1985, 18, 95. Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. Comprehensive review: Berks, A. H. Tetrahedron 1996, 52, 331 and references cited therein.
4. 2. Murahashi, S.; Naota, T.; Kuwabara, T.; Saito, T.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1990, 112, 7820. Murahashi, S-I.; Saito, T.; Naota, T.; Kumobayashi, H.; Akutagawa, S. Tetrahedron Lett. 1991, 32, 5991.
5. 2. Murahashi, S.; Naota, T.; Kuwabara, T.; Saito, T.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1990, 112, 7820. Murahashi, S-I.; Saito, T.; Naota, T.; Kumobayashi, H.; Akutagawa, S. Tetrahedron Lett. 1991, 32, 5991.
6. 3. a) Evans, D.A.; Sjogren, E.B. Tetrahedron Lett. 1986, 27, 4961.
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9. d) Seki, M.; Yamanaka, T.; Miyake, T.; Ohmizu, H. Tetrahedron Lett. 1996, 37, 5565.
10. 4. Cainelli, G.; DaCol, M.; Galletti, P.; Giacomini, D. Synlett 1997, 923; Cainelli, G.; Giacomini, D.; Galletti, P.; DaCol, M.; Tetrahedron: Asymmetry 1997, 8, 3231; Cainelli, G.; Galletti, P.; Giacomini, D. Synlett 1998, in press.
11. 4. Cainelli, G.; DaCol, M.; Galletti, P.; Giacomini, D. Synlett 1997, 923; Cainelli, G.; Giacomini, D.; Galletti, P.; DaCol, M.; Tetrahedron: Asymmetry 1997, 8, 3231; Cainelli, G.; Galletti, P.; Giacomini, D. Synlett 1998, in press.
12. 4. Cainelli, G.; DaCol, M.; Galletti, P.; Giacomini, D. Synlett 1997, 923; Cainelli, G.; Giacomini, D.; Galletti, P.; DaCol, M.; Tetrahedron: Asymmetry 1997, 8, 3231; Cainelli, G.; Galletti, P.; Giacomini, D. Synlett 1998, in press.
13. 5. Methyl (R)-3-hydroxy-butyrate is the starting material for the industrial production of 1: Nakatsuka, T.; Iwata, H.; Tanaka, R.; Imajo, S,; Ishiguro, M.; J. Chem. Soc., Chem. Comm. 1991, 662. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
14. 5. Methyl (R)-3-hydroxy-butyrate is the starting material for the industrial production of 1: Nakatsuka, T.; Iwata, H.; Tanaka, R.; Imajo, S,; Ishiguro, M.; J. Chem. Soc., Chem. Comm. 1991, 662. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134.
15. 6. Kamiya, T.; Hashimoto, M.; Nakaguchi, O.; Oku,T. Tetrahedron 1979, 35, 323
16. 7. The most convenient methods to obtain the (R)-3-hydroxybutyric acid are available either through depolymerization of poly-(R)-3-hydroxybutyrate (see: Seebach, D.; Roggo, S.; Zimmermann, J., in: Stereochemistry of Organic and Biorganic Transformation. Bartmann, W.; Sharpless, K. B., Eds., Vertag Chemie, Weinheim 1987, pp. 85-126) or by microbial oxidation: Ohashi, T.; Proc. CHIRAL 90 SYMP., Spring Innovations, Stockport, UK, 1990, pp.65-71.
17. 7. The most convenient methods to obtain the (R)-3-hydroxybutyric acid are available either through depolymerization of poly-(R)-3-hydroxybutyrate (see: Seebach, D.; Roggo, S.; Zimmermann, J., in: Stereochemistry of Organic and Biorganic Transformation. Bartmann, W.; Sharpless, K. B., Eds., Vertag Chemie, Weinheim 1987, pp. 85-126) or by microbial oxidation: Ohashi, T.; Proc. CHIRAL 90 SYMP., Spring Innovations, Stockport, UK, 1990, pp.65-71.
18. 8. Ireland, R. E.; Wardle, R. B.; J. Org. Chem. 1987, 52, 1780.
19. 3, 75.5 MHz): 164.5; 155.8; 132.1; 117.3; 114.2; 65.7; 56.5; 55.7; 40.6; 25.6; 20.7; 17.8;-4.2;-5.0.
20. 10. Intermediate 1 is purchased from Aldrich.
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22. 12. Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C.; J. Am. Chem. Soc. 1993, 115, 995. Löpez, R.; Sordo, T.L.; Sordo, J.A.; Gonzalez, J.; J Org. Chem. 1993, 58, 7037. Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D.C.; J. Am. Chem. Soc. 1991, 113, 5784.
23. 12. Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C.; J. Am. Chem. Soc. 1993, 115, 995. Löpez, R.; Sordo, T.L.; Sordo, J.A.; Gonzalez, J.; J Org. Chem. 1993, 58, 7037. Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D.C.; J. Am. Chem. Soc. 1991, 113, 5784.
24. 12. Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C.; J. Am. Chem. Soc. 1993, 115, 995. Löpez, R.; Sordo, T.L.; Sordo, J.A.; Gonzalez, J.; J Org. Chem. 1993, 58, 7037. Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D.C.; J. Am. Chem. Soc. 1991, 113, 5784.